Character Analysis
The Widower
Everyone could use a Sean Maguire in their lives.
This guy lost his wife to cancer a few years before this movie starts, and he loves her more than we love Matt Damon with a Boston accent. When Will starts pushing his buttons, asking if his wife was ever unfaithful, he loses his cool:
MAGUIRE: If you ever disrespect my wife again, I will end you, I will f***in' end you. Got that, chief?"
Show him who's boss, Sean.
Of course, most therapists would probably throw Will out of their office at this point—but not Maguire. He recognizes that there's something inside Will that's making him...do what he does. And he wants to get to the bottom of it.
After causing the initial kerfluffle, Sean's wife ends up being what brings Maguire and Will together.
Will asks Sean if he ever regrets meeting his wife—you know, because of the pain he feels now that she's gone. Of course, what Will's really asking is this: is it worth it to put your heart on the line if there's a chance you might get hurt?
Sean's answer?
MAGUIRE: I don't regret the eighteen years I was married to Nancy. I don't regret the six years I had to give up counseling when she got sick. And I don't regret the last years when she got really sick.
Translation: yes.
Totally worth it.
Maybe a little personal for a therapist, but by talking about his personal experience, Maguire is able to build trust with Will while showing him a good example of how to be vulnerable around the people we love.
Lifestyle Philosopher
It's not easy for Maguire to be Will Hunting's therapist, what with Professor Lambeau always breathing down his neck. The fact is that Maguire and Lambeau have completely different views on what it is to live a good life. For Lambeau, living a good life means fulfilling your intellectual potential, which is why he wants Will to work at a prestigious think tank. But for Maguire, the good life means making the decisions that are right for you… and not necessarily right for others.
When Lambeau challenges him on his philosophy, Maguire asks Lambeau to understand Will's situation:
MAGUIRE: Why is he hiding? Why doesn't he trust anybody? Because the first thing that happened to him, he was abandoned by the people who were supposed to love him most.
Lambeau thinks this is all just a bunch of sentimental nonsense, but Maguire insists that Will's life will be ruined if Lambeau pushes him too hard to be some big mathematical superstar. Lambeau's biggest problem is that he can only see the world through his own vision of success, while Maguire is willing to help Will figure out his own definition of success.
Therapist or Friend?
Sean Maguire is kind of a foil for Will, showing the audience what it looks like to experience things instead of just read about them, like Will does.
MAGUIRE: You've never held your best friend's head in your lap, and watched him gasp his last breath looking to you for help.
Maguire has been in the Vietnam War—the guy knows what it's like to watch someone die. Will, on the other hand, has only learned things from books; he's too scared to go out into the world and experience things for himself. Maguire spends the movie trying to get Will to open himself up to new experiences, sometimes by giving him the love he needs, and other times by straight up real talking:
MAGUIRE: You and your bulls***. You got a bulls*** answer for everybody. But I ask you a very simple question and you can't give me a straight answer.
By the time the movie ends, Maguire's combination of trust and straight-talk has help transform Will. But don't forget: it's also helped transform Maguire himself. The dude realizes he needs to take his own advice and start living again instead of sitting around feeling sorry for himself over losing his wife. As he tells Will,
MAGUIRE: Yeah, you know, I figured I'm just gonna put my money back on the table and see what kinda cards I get. You do what's in your heart son, you'll be fine.
As different as they are, it turns out Maguire and Will both needed to learn the same lesson.
Two peas in a pod, eh?